How to Handle Tricky Friend Situations

Save your friendship by dealing with annoyances gracefully

You love your best friend—but you can do without her offensive husband. Or maybe you adore spending time with her—but are getting tired of all the times she "forgets" her share of the bill. If you find yourself swallowing your true feelings in order to keep the peace, you're not alone. "Often, women have a hard time being direct," says Debra Holland, PhD, a Los Angeles–based psychotherapist. Instead, we tend to absorb the anger, annoyance or whatever until we get upset—but that's not healthy for you or your relationship. If you value your friend and want to keep her in your life, it's important to learn how to be honest without offending her. Below, check out eight tricky situations you can get into with friends, and how to resolve them without losing the friendship.

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Situation #1: She's Judgmental of Others

You two are at a party together, and your pal comes out with comments about others that make you cringe, like, "What the heck is that woman thinking wearing that dress?" What's worse, she's often judgmental about people you're both friends with. Friendship-saving strategy: Speak to her, in the moment, with genuine curiosity (rather than using judgment yourself), by saying something like, "Did you mean to be so critical? Because you sounded that way," suggests Dr. Holland. "That gives her a chance to save face. She may not acknowledge it, but she's now aware of it." Photo: Winston Davidian / Getty Images

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Situation #2: You Always Pay the Bill

Did she forgot to stop at the ATM again?! After covering the tab for the umpteenth time, you're getting sick of ponying up for lunch. Friendship-saving strategy: First, think about what your part has been in this situation, says New Jersey–based psychotherapist and coach Beth Tunis. "If you've been letting it go over and over, she may have no idea that it's a problem." Then, consider what you're going to say to her the next time you two make plans. Try something like, "The last time we had lunch, I ended up picking up the check, which was fine at the time, but I can't always do that. Do you maybe want to go somewhere less expensive?" That gives her space to admit that she felt bad last time, or that she actually didn't notice, or that she is having financial issues. Whatever her reasoning, clearing the air is best, because resentment can be toxic to a friendship. Photo: Gazimal / Getty Images

Situation #3: She Puts You in the Middle of Her Fights

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Your friend is in a snit with another friend, and she's trying to drag you over to her side. Yet you know just enough about the situation to realize that your pal is not 100 percent in the right—or the wrong. Friendship-saving strategy: Nothing good can come of you playing monkey in the middle, says Tunis. "Pull yourself out of it by saying, 'You know, I think this is between you and Sarah,' then change the subject." Hopefully that will send her the message that you don't want the blow-by-blow of their argument. That said, a good friend will respond to her feelings about the fight: "I know you're frustrated by the situation with Sarah. That must feel awful." The idea is to support her without getting intimately involved. Photo: Karen Moskowitz / Getty Images

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Situation #4: You Heard Her Spouse Is Cheating

This is a toughie, for obvious reasons—you don't want to be the messenger who gets shot for delivering bad news, but you also can't bear the thought of your friend being unknowingly betrayed. Friendship-saving strategy: "Think hard about what you would want if you were in her shoes," says Dr. Holland. "Chances are, you'd want to know." In that case, you have to tell her, gently, with something like, "I have something to say that's going to be difficult for you to hear. This is what I've seen/heard." Then be prepared to support her no matter how she reacts—she may already know but not want to face it yet, or she may be angry with you at that moment. "If she says she doesn't want to talk about it, leave it there until she's ready to," says Dr. Holland. Photo: Karen Moskowitz / Getty Images

Situation #5: She's in Debt but Keeps Shopping

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One day, she's moaning to you about how tight money is and how she's juggling multiple overstretched credit cards. The next, she's telling you about her hot new boots. Friendship-saving strategy: "There are two schools of thought here," says Tunis. "One, that it's none of your business; two, that a good friend needs to intervene." So first decide how you want to act. If you feel you have to do something, "don't tell her what she should do, but make yourself an example: 'I saw these shoes and love them, but I'm on a budget,'" advises Tunis. To keep yourself from getting frustrated while watching her shop and holding your tongue, avoid shopping with her, Tunis adds. Photo: Bounce / Getty Images

Situation #6: You Don't Like Her Husband

He's a boor, he drinks too much, he makes racist or sexist remarks…pick your reason, but the fact remains that you have no desire to spend time with your friend's significant other. Friendship-saving strategy: Choose to spend time with your friend without her husband, says Tunis. If she calls to invite you to go to dinner as a foursome and you can't stomach it, say something like, "How about we go get a manicure and lunch, just us, instead? I feel like we're always going out as couples and I want to spend time with you alone." However, if you're close to them as a couple and her hubby says something offensive, "you may want to speak up, saying, 'I find comments like that upsetting,'" suggests Tunis. You might have to deal with your friend's disapproval or anger, but some things need to be said. Photo: Hemera Technologies

Situation #7: She Dresses Inappropriately

Did she show up at your very conservative sister's bridal-shower tea in a slinky mini-dress and stilettos? Yikes. Friendship-saving strategy: If you know she has a penchant for embarrassing herself with poor fashion choices, give her the tools beforehand to make better ones: "I've heard that the office holiday party is business dress. What are you wearing?" This may be especially important if it's your function and it's important that she dresses appropriately, or if you know it'll harm her in some way (say, at that office party, if you know the boss is disapproving). Photo: Jupiterimages

Situation #8: She's About to Make a Bad Decision

Your pal calls you excitedly to tell you she's about to plunk down half her savings on what you feel is a dubious investment, or is thinking of having a fling with her married coworker. Friendship-saving strategy: You want to give her information that she may find useful ("I've read about that company; I don't think they're on such solid ground"), but not judge her. Instead of busting out with "Are you crazy?", try to come across with concern, not criticism. Share what you're worried about, says Dr. Holland: "I'm concerned that if you do this, XYZ might happen." Photo: iStockphoto